89374-79-8Relevant articles and documents
Diels-Alder Reaction of 2-Vinylindoles with Maleic Anhydride
Narasimhan, N. S.,Kusurkar, R. S.,Dhavale, D. D.
, p. 1004 - 1010 (2007/10/02)
N-Methyl-2-(2-methyl- (1), 2-methoxy- (2), and 2-ethoxycarbonyl- (3) -vinyl)indoles furnish the corresponding Diels-Alder adducts 5, 6 and 7 when treated with maleic anhydride.Under similar conditions N-methyl-2-(2-nitrovinyl)indole (4) undergoes dimerisation to give the dimer (8).Dimerisation to compound 17 is also observed during attempted separation of the mixture of cis- and trans-isomers of N-methyl-2-(2-methylvinyl)indole (1) on silica gel.The Diels-Alder adducts (5 and 7), on hydrolysis, followed by lead tetraacetate oxidation give the carbazoles, 11 and 14a + 14b respectively.